Withanolides
Withanolides are a group of at least 300 naturally occurring chemical compounds . Chemically, they are lactones with 28 carbon atoms linked to a steroid structure or their lactols or seco derivatives ; they are created by the oxidation of steroids.
Occurrence
As secondary plant substances, they are mainly found in various genera of the nightshade family , for example in the Tomatillo and the eponymous Withania . The benefits withanolides to the plant appear to be varied; In any case, some of the substances keep insect larvae from eating the plant. Several withanolides showed medically interesting effects for humans in the laboratory.
In the meantime, 13 genera of the nightshade family are known in whose species withanolides occur, some of them: thorn apples ( Datura ), dunalia , violet bushes ( Iochroma ), box thorns ( Lycium ), poisonous berries ( Nicandra ), bladder cherries ( Physalis ), salpichroa , nightshade ( Solanum ) , Withania , Jaborosa .
Examples
Withaferin A from sleeping berries ( Withania somnifera ) was the first withanolide to be isolated. An anti-inflammatory effect of various withanolides of the plant could be shown in animal experiments; several dozen are known. The plant is known in Ayurvedic medicine under the Sanskrit name Ashwagandha .
Salpichrolide A, B and G (from Salpichroa origanifolia ) inhibit the growth of larvae of the Mediterranean fruit fly ( Ceratitis capitata ). They are therefore of interest for agriculture.
The nicandrenones from the poison berry ( Nicandra physalodes ) are another group of withanolides with an insecticidal effect. They were examined 30 years ago; the first total synthesis succeeded in 2000.
Ixocarpalacton A from the Tomatillo ( Physalis philadelphica ) is a promising substance for preventing cancer.
Individual evidence
- ↑ Rudolf Hänsel, Otto Sticher: Pharmakognosie - Phytopharmazie. 9th edition, Springer-Verlag, 2009, ISBN 978-3-642-00962-4 , p. 844.
- ↑ Synthesis, structure and conformation of natural products and analogues of biological importance Research Group ( Memento of the original from January 2, 2007 in the Internet Archive ) Info: The archive link has been inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice.
- ↑ Drugs.com: Ashwaganda
- ^ S. Bado et al .: Lethal and Sublethal Effects of Withanolides from Salpichroa origanifolia and Analogues on Ceratitis capitata. J. Agric. Food Chem, 52/10/ 2004 . Pp. 2875-8. doi : 10.1021 / jf035508a
- ↑ BM Stolz, T. Kano and EJ Corey: Enantioselective Total Synthesis of Nicandrenones. JACS 122 / - / 2000 . Online PDF ( Memento of the original from June 23, 2010 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice.
- ^ AD Kinghorn et al .: Cancer Chemopreventive Agents Discovered by Activity-Guided Fractionation: An Update. Current Organic Chemistry. 7/3/ 2003 . Pp. 213-226. Abstract
